And leslie t



umrso STATES PATENT. OFFICE.

HAROLD I. caravans; or 'nouimnsoox, IIIW JERSEY, am) mean: 1'. surnnnnm.

OI KAI-MA, m YOBK LBSIGNORS TO THE QLYBYN CORPORATION, 01 NEW YORK- JI. Y., A OORPOEL'IIOR 01 NEW YORK rnocsss 30B GHLORDI'A'I'ING EYDBOOLBZBORB.

He Drawing.

To all whom it my mom.-

Be it linown that we, no F. Serm- 'nrms, residing at Bounflbrook, in the county one and particularly to the production of trichlorhydrin or tri'chlo ropane. We have found that upon treating the dichlor addition product of pro ylene, propylene chlorid, with chlorin in t 0 presence of the chlorin carriers or catalysts asordinaril used, i; e. iodin ehlorid, phosphorus,'aluminum chlorid, etc, the reaction does not ceed satisfactorily to the symmetrical trichlorhydrin. 'On the contrary, with this rocedure, isomeric com ounds are formed in large proportion, which prevent a ood ield of the symmetrical trichlorhy rin. urthermore, the reaction is extremely slow,

and it is practically impossible to completely separate the catalyst or chlorin carrier used from the product by repeated distillations. We have found, however, that these objectionable features may be overcome by the use of'eertain sous sulfur compounds asfe'a'talysts or ch orincarriers. We have found that when small proplclirotions are used of sulfur dioxid, sulfur c ridsor sulfu'ryl chlorid as the catalyst, there is a great im rovement. in the 'epeed'of the reaction and t 'e chlorination proceeds practicall quantitatively to the formation of trich orhydrin according ,to the equation The dry hydrochloric acid leaves the solution as a gas. together with the sulfur dioxid,

ipeclncatlcn of Letters Patent. Application ans Arrest at, me. sum In; 407,105.

ene chlori from the unchanged Patented Dec. 14. 1920.

ing the o oration under the influence of' actinic lig t, that is, in direct sunlight or in the rays of a flaming are or ultra violet liglgz.

, e have found that the various gaseous sulfur. compounds referred to are all extremely effective, sulfur dioxid bein per haps best ada ted for the purpose. preferred metho for earryin out the reaction 18 add sulfur dioxid an chlorin in separate streams to the pro ylene chlorid in the presence of direct eu ight or the re s of n. fiannn arc, the prop lenechlorid hein contains within a suite le glass vessel. 1% second method is to mix the sulfur dioxid with 'thg chlorin and ass the mixtm-e throughpropylene chlori The-process ma be carried out at room t'em rature or at igher tem erature, if desire The quantit of the su fur compound required is extreme y small. We have found that sulfur'dioxid is effective in the proportion of one-half of one per cent. of the chlorin added to the pro ylene chlorid.

We'have found that t e process described me be effectively practised on a commercia scale with the advantageous features that thespeed of reaction is increased the production of isomeric compounds is iminated and that thereaction proceeds smoothly without explosions.

.What we claim is:

1 A process cfproducing trichlorhydrin, which CDIDJH'ISBS adding'chlorin to propylin the presence of a gaseous sulfur compound, as a catalyst.

2. A process of producing trichlorhydrin, which'oomprises adding ch orin to propylene chlorid in the presence of sulfur dioxld,

as a catalyst.

3. A p of producing a chlorin substitution roduct of propylene, which com prises ad mg chlorinto propylene chlorid m the presence of a gaseous sulfur comimd as a catalyst, and se aratixag the .product formed from any unc ange propylene chlorid by distillation.

4. A process of reducing a chlorin substitution roduct o propylene, which comprises ad ing ehlc'rin to propylene chlorid 100 in the.

ound he i 01106.

pnses-ad compound in aeparata streams to ..PI'QOB83 6 sti utipn mine 5 m 01 a mou 'nulfur' m a process b61113 cam 61 mania light.

ed "out under chlorin flabt Of prop lens, which comagaseous sulfur l cblorid, -in the preaenoe'df actinic gm ene chlori sulfur compound in a oeeding on; par cent. 0

the

triohlor orin topgopylin the presence of p gaseous fpropprtion not ex- .qhlor'in added This specification lignd and witnessed this 10th day 9f Augqsq'lm.

I HAROLD F. SAUNDERS. Witness;

flhis speqifiodtioqsigngd and witnessed thl8'27th day of Aiigust 1920.

, LESLIE T. EUTHERLAND. Witnesses:

Tnoma Lomam, M. J. Tunon. 

